US3725455A
Expired / Lapsed
US
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Peroxy compounds containing a carbonate group
Assignee: Pennwalt Corp
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Filing: 1968-06-17
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Granted: 1973-04-03
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Expires: 1988-06-17
Abstract
Abstract A new class of compounds: R-W-R'' where R and R'' are identical oxy radicals containing peroxide functions such as dialkyl or diaralkyl peroxide, peroxyketal, peroxyester, or monoperoxycarbonate, and W is a carbonyl group, or carbonyl containing group, or an alkylidene or aralkylidene group, or a phosphorus containing group. Examples: Di(1,3-dimethyl-3-(t-butylperoxy)butyl) carbonate; Di(1,3-dimethyl-3-(n-butoxycarbonylperoxy)butyl) carbonate; 2,2-Bis(3,3-di(t-butylperoxy)butoxy)propane; Di(1,3-dimethyl-3-(t-butylperoxy)butyl) ethyl phosphate. They are free radical affording compounds useful in crosslinking of polyolefins and unsaturated polymers, and for the polymerization of vinyl monomers and diolefinic monomers.
Inventors
- 👤 C Sheppard
- 👤 Angelo A D
- 👤 O Mageli
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 14:30
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/04; C08K5/14; C07; C07C; C07C407/00; C07C409/00; C07C409/16; C07C409/20; C07C409/22; C07C409/38; C08F; C08F283/00; C08F283/01; C08F4/00; C08F4/28; C08F4/32; C08F4/38; C08G; C08G18/00; C08G18/06; C08G18/83; C08G18/86; C08K5/0008; C08K5/0025
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
8 words
Claim 1 wherein said peroxide is di(2-(t-butylperoxy-carbonyl)-ethyl) carbonate.
Claim 2
Dependent Claim
8 words
Claim 1 wherein said peroxide is di(1,3-dimethyl-3-(n-butoxycarbonylperoxy)butyl) carbonate.
Claim 3
Dependent Claim
60 words
A process for preparing coupled peroxy compounds of claim 1, which process comprises: a. reacting, at a temperature of from -10* C. to not more than 100* C., about two moles of a hydroxy-containing peroxide with about one mole of a hydroxy coupling agent selected from phosgene and bischloroformates, and b. recovering the coupled peroxy compound from the reaction mixture.
Claim 4
Dependent Claim
112 words
A process for preparing coupled peroxy compounds of claim 1 by the interaction of a hydroxy-containing peroxide with a hydroxy coupling agent selected from phosgene and bischloroformates, which process comprises: a. reacting one molar equivalent of said hydroxy-containing peroxide with said hydroxy coupling agent at a temperature of from about -10* to +25* C. to form an intermediate peroxy compound; b. reacting said intermediate compound at a temperature of not more than 100* C. in an amount sufficient to couple with a compound selected from the class consisting of dihydroxy compounds and said hydroxy-containing peroxide to form a coupled peroxy compound; and c. recovering the coupled peroxy compound from the reaction mixture.
Claim 5
Dependent Claim
2 words
Di(1,3-dimethyl-3-(t-butylperoxy)butyl) carbonate.
Claim 6
Dependent Claim
2 words
Di(4,4-di(t-butylperoxy)pentyl) carbonate.
Claim 7
Dependent Claim
3 words
Ethylene Bis(1,3-dimethyl-3-(t-butylperoxy)-butyl carbonate).
Claim 8
Dependent Claim
68 words
A process for the preparation of di(1,3-dimethyl-3-(t-butylperoxy)butyl) carbonate which process comprises: a. intermixing, at a temperature of about 5* C. in the presence of a base, one molar equivalent of phosgene and two molar equivalents of 2-methyl-2-(t-butylperoxy)-4-pentanol; b. increasing the reaction temperature gradually to not more than about 50* C., for a time sufficient to complete the reaction; and c. recovering the wanted product from the reaction mixture.
Claim 9
Dependent Claim
82 words
A process for the preparation of ethylene bis(1,3-dimethyl-3-(t-butylperoxy)butyl carbonate) which process comprises: a. reacting at a temperature of about 5* C. equimolar amounts of phosgene and 2-methyl-2-(t-butylperoxy)-4-pentanol, to form 1, 3-dimethyl-3-(t-butylperoxy)butyl chloroformate; b. reacting, at a temperature of about 20* to 25* C. and in the presence of a base two molar equivalents of said peroxy containing chloroformate and one molar equivalent of ethylene glycol, for a time sufficient to complete the reaction; and c. recovering the product from the reaction mixture.
Claim 10
Dependent Claim
92 words
A process for the preparation of a coupled peroxy containing compound which process comprises: a. reacting one molar equivalent of hydroxy-containing peroxy compound with phosgene at a temperature of from about -10* to +25* C. to form an intermediate peroxy containing chloroformate compound; b. admixing equimolar amounts of said peroxy containing chloroformate compound and a tertiary-amine; c. adding water at a rate and temperature sufficient to control the evolution of carbon dioxide; d. continuing the reaction until the evolution of carbon dioxide ceases; and e. recovering the product from the rEaction mixture.
Claim 11
Dependent Claim
83 words
A process for the preparation of di(1,3-dimethyl-3-(t-butylperoxy)butyl) carbonate which process comprises: a. reacting at a temperature of about 5* C. equimolar amounts of phosgene and 2-methyl-2-(t-butylperoxy)-4-pentanol, to form 1, 3-dimethyl-3-(t-butylperoxy)butyl chloroformate; b. admixing equimolar amounts of said peroxy chloroformate and pyridine at about 23* C.; c. adding water at a rate sufficient to control the evolution of carbon dioxide; d. continuing the reaction at about 23* C. until the evolution of carbon dioxide ceases; and e. recovering the product from the reaction mixture.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1976-04-02 | 1976-10-02 | 1977-04-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1980-04-02 | 1980-10-02 | 1981-04-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1984-04-02 | 1984-10-02 | 1985-04-03 | $7700.00 | Window Closed / Lapsed |